Two older women with short grey hair smiling and talking. Text over the image says "The Art of Listening and Probing: Building Stronger Donor Relationships."

The Art of Listening and Probing: Building Stronger Donor Relationships (Part 2)

Last week in our blog, we talked about the purpose of questions and gave advice on how to talk less and listen more. Today we will cover how to dig deeper in your donor conversations by “drilling down.”

Ask, Then Drill Down

Asking your donor about a topic and following up with a question related to what they just said demonstrates active listening and encourages more dialogue. Remember, asking questions, particularly follow-up questions, increases how likable you are. Follow-up questions show that you are interested and care, which makes for better conversation and a stronger relationship with your donor.

It usually takes more than one question to truly investigate a topic, especially when it comes to your donor’s connection to your organization or their feelings about philanthropy in general.

Once you uncover a topic of interest, you’ll want to drill down to explore their point of view further. The more you know about your donors’ passions, goals, concerns and frustrations, the better you will be able to propose an appropriate gift opportunity.

Sample Drill-Down Questions

Here are some questions to get you started drilling down.

  • “How long have you been thinking about this?”
  • “I’d love to hear more about that.”
  • “I’m a little unclear. Can you explain it further?”
  • “Why is this important to you?”
  • “What happens if you…?”
  • “How does that impact you (and your family/spouse/children/grandchildren)?”
  • “Can you give me an example?”
  • “What have you done in the past in that type of situation?”
  • “What do you have in mind?”
  • “What could we have done better?”
  • “Can you tell me more about that?”
  • “How did you feel about that?”
  • “Why is that important to you?”
  • “What (or who) influenced your thinking on this?”

One-Word Drill-Down Questions

Sometimes all you need is a word or gesture to prompt your donor to continue speaking. Important: Be sure to pause afterward. You’ll find that silence is an unlikely source of power. It may make you a bit uncomfortable at first, but it gets easier the more you practice it. Here are a few to get you started:

  • “Really?” (head tilt)
  • “Interesting.” (nodding)
  • “Wow!” (smiling, eyebrows raised)

Remember your body language can say as much as your words. Practice a donor conversation with a colleague and ask for their feedback on what felt good to them and what didn’t. Record the practice session so you can watch it back to pick up on any body language habits that you aren’t aware you have (clicking a pen, touching your hair, tapping your foot) and any filler words you might tend to use more than you would like to (um, like, I mean).

Next week we will explore rephrasing and open- and closed-ended questions.

In the meantime, we have a couple of past webinars with lots more tips on making your donor conversations more productive:

Gregory J. Sharkey, J.D., Senior Philanthropy Advisor at The Nature Conservancy, teaches you how to spark conversations that lead to gifts through a thoughtful series of tried-and-true questions.

Questions to Start Gift Planning Conversations

Scott Lumpkin, gift planning expert and philanthropic advisor, teaches you how to recognize and overcome the roadblocks keeping you from understanding and communicating effectively with your donors.

Learning to Speak Gift Planning

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